Literature DB >> 17935353

Highly diastereo- and regioselective transition metal-catalyzed additions of metal hydrides and bimetallic species to cyclopropenes: easy access to multisubstituted cyclopropanes.

Alexander Trofimov1, Marina Rubina, Michael Rubin, Vladimir Gevorgyan.   

Abstract

The first highly efficient, diastereo- and regioselective transition metal-catalyzed addition of metal hydrides (stannanes, silanes, and germanes) and bimetallic species (ditins and silyltins) to cyclopropenes has been developed. It was shown that the addition across the double bond of cyclopropenes is generally controlled by steric factors and proceeds from the least hindered face. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted stereodefined cyclopropylmetals, useful building blocks unavailable by other methods.

Entities:  

Year:  2007        PMID: 17935353     DOI: 10.1021/jo701855c

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  Directed nucleophilic addition of phenoxides to cyclopropenes.

Authors:  Pavel Yamanushkin; Michael Lu-Diaz; Andrew Edwards; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2017-10-04       Impact factor: 3.876

2.  NHC-Ni(II)-catalyzed cyclopropene-isocyanide [5 + 1] benzannulation.

Authors:  Jian-Qiang Huang; Meng Yu; Xuefeng Yong; Chun-Yu Ho
Journal:  Nat Commun       Date:  2022-07-16       Impact factor: 17.694

3.  Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.

Authors:  Vinod Tarwade; Ramajeyam Selvaraj; Joseph M Fox
Journal:  J Org Chem       Date:  2012-10-19       Impact factor: 4.354

4.  Directed carbozincation reactions of cyclopropene derivatives.

Authors:  Vinod Tarwade; Xiaozhong Liu; Ni Yan; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2009-04-22       Impact factor: 15.419

5.  Intramolecular nucleophilic addition of carbanions generated from N-benzylamides to cyclopropenes.

Authors:  Vladimir Maslivetc; Colby Barrett; Nicolai A Aksenov; Marina Rubina; Michael Rubin
Journal:  Org Biomol Chem       Date:  2018-01-03       Impact factor: 3.876

6.  Copper-Catalyzed Enantio- and Diastereoselective Addition of Silicon Nucleophiles to 3,3-Disubstituted Cyclopropenes.

Authors:  Liangliang Zhang; Martin Oestreich
Journal:  Chemistry       Date:  2019-10-22       Impact factor: 5.236

  6 in total

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